Nongovernmental 457b disbursement question

[akchang]

Hi.  I'm 52 years old, in the 32% tax bracket, and have been thinking more and more about retiring early.  In the meantime, I have two 457B plans that are non-governmental.  It's also possible I might be taking a new job.  This new place has a 457b plan but doesn't accept old ones (and neither did my second job accept the first job's 457b).  My first job's 457b has around $250k in it.  I've managed to keep it there for a while but it looks like I may have to have it distributed based on a change in employment status.  I might also have to do the same with my other 457b if I move to this new job, though this second 457b is much smaller. 

I have several options, including delaying to a specific date, electing a lump sum, or electing periodic installments.    For sake of argument, let's say I decide to do a lump sum and have the money to pay for the taxes.  After I've done that, can I take all the original 457b corpus and put it into my Roth account? If so, can I do this directly by rolling it over into the Roth account and paying taxes (or are there required intermediate steps?). Although it will be a big tax hit, I figure it will give that corpus more time to compound in the Roth account and tax rates are going way up in the future anyway.  But let me know if you don't think this would be a wise move or if there are alternative strategies I should be investigating.

Thanks.  I just recently found your site and look forward to learning a ton more.

[gocurrycracker]

A few things to unpack here and I am replying in my phone so please forgive the brevity

Tax rates may go up in the future, yes. But unlikely on people making <$200k/year. Debate that number as much as you like, but we have a progressive tax system and people at the bottom have low or zero tax bills. That won’t change because you can’t squeeze blood from a stone

Lump sum distributions are inherently tax unfriendly. Compare the taxes of just doing 2 distributions, one on Dec 31st and another on Jan 1st. The tax bill would be less than half. Now distribute over 10-20 years...

Mathematically, there is no advantage to front-loading the taxes. You will end up with more $ by doing it over time. The way to compare this is to look at the marginal tax rate on each transaction.